Looking for love? Hire a wingwoman

I spent an evening stalking a professional wingwoman and her client (don't worry they knew I was following them).

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It’s a warm Thursday night in New York City and I’m doing my best to discreetly stalk a couple that just met outside a downtown bar. As they hop from bar to bar looking for a place to land, I keep a good six yards behind them. All the while they’re strolling together with a good foot of space between them.

The pair, “C” and “Jay,” knew that I was following them, so there’s no need to call NYPD on me — for this, at least. I was hitching along for the evening and watching as C, whose services run about $82 per hour (with a two-hour minimum) helps Jay meet women and get their numbers.

C works for a New York City and Boston-based dating service called Hire a Wingwoman and is one of several professional wingwomen who range from at least 21 to as old as 50.

Susan Baxter, Hire a Wingwoman’s founder, said the idea for the service originated from her own personal experiences as a wingwoman.

“It can be hard to approach that intimidating hot girl across the bar,” Baxter explained. “It's so much easier to have an outgoing socialite go up to people for you and talk you up. I just thought that this is a real business, and this is something people need.”

C is the perfect example of the outgoing socialite that Baxter advertised: young, fashionable, personable and attractive.

"You have to talk to people. You have to break the ice. You have to get people to get their guard down and be nice back,” C said when I asked her what made a good wingwoman. “You've got to have confidence to just go out there and just start talking to random people. It's a different type of personality, but I think New York is the perfect place for that.”

C, who works in advertising by day, has been with Hire a Wingwoman since the company moved to New York City nearly a year ago. None of her friends or family know that about her work as a Wingwoman.

“It just hasn’t come up,” C told me. “I think I would tell my friends. I probably wouldn't tell my family because I don't think they would understand. They don't live in New York — they live in the suburbs of Florida; they're super old-fashioned. It's not like I feel embarrassed.”

When C and Jay finally picked a place, I grabbed a beer and planted myself against a wall. Jay was on his phone and C was looking at the drink menu on the wall. I looked down for a second and when I looked up C was talking to two women sitting at the bar.

"The friend had cool leopard shoes on," C recounted to me later on in the night. "I was like 'Those are so cool! I want those! Where are they from?' She told me this whole story … She was very bubbly.”

C also explained that along with her shoe compliment, C told a made up story about how she had just moved to New York and was looking around for places “to have fun.”

“How much do you really have to gamble on the woman being bubbly like she was?" I asked.

"I got lucky. I got really lucky. In my position I have nothing to lose. I just keep going until there's nothing left. If she wasn't so bubbly I would have probably told my story anyway and tug at some heart strings y'know? Get them to open up."

I watched as all this happened from across the bar: the swoop, the compliment, the story and as soon she earned their trust, the gentle and casual introduction of Jay into the conversation

Jay is a good-looking man of average height in his early 30s who works in the medical field. This was Jay’s first time going out with C but his second session with Hire a Wingwoman.

Jay arrived to his night out with C wearing his scrubs, which struck me as both odd and slightly genius.

“Women are supposed to love doctors,” I thought in my head. “Lord knows I do.”

Speaking with Jay earlier I gathered that he had no lack of confidence, and seemed like a smart and outgoing guy. When I asked why he needed a wingwoman to help him talk to women he told me it was to “get an in.”

“It's always the guy’s role to initiate and I have no problems doing that,” Jay conceded. “It's not hard to do, it’s just not everyone is receptive when it's a guy.”

Jay went on to explain that the wingwoman gives him a better rapport with women who would write him off as creepy if he approached them in a bar.

“Yes, it might seem a little odd at first but I feel like all is fair in love and war,” Jay says in defense. “If you don’t want to want to sell yourself short and get what you want, you have to do what it takes.”

I did my best to discreetly watch Jay talk up the women from across the bar, although I realized my “casual” spot standing between two full tables made me stick out like like a cowlick. So I casually made my way over and sat next to them and watched from the corner of my eye.

What intrigued me the most about this stage of the evening was watching C slowly pull back from the group after introducing Jay.

She buoyed herself as far she physically could without looking out of place all the while paying very close attention the conversation. There was no doubt that she getting ready to swing in the moment she sensed Jay struggling.

Luckily for her, Jay was doing just fine.

"I saw him hitting it off so I backed up a little bit just to give him some space, see where it was going.” C explained after we left the bar. “I saw it was going well so then I went to occupy the friend."

“High five for that one,” Jay prompted, which made C laugh.

“Did you end up getting her number?” I asked Jay.

He grinned casually, “I did.”

Matt Lee is a Web producer for Metro New York. He writes about almost everything and anything. Talk to him (or yell at him) on Twitter so he doesn’t feel lonely @mattlee2669.